2-[4-(2-Benzyloxyacetylamino)phenoxy]propionic acid methyl ester → 2-[4-(2-Hydroxyacetylamino)phenoxy]propionic acid methyl ester

HRID 2169745Notes

Reaction equation

HRID 2169745 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:24])[CH2:15][O:16]CC2C=CC=CC=2)=[CH:9][CH:8]=1)[CH3:5]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:25])[CH:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:24])[CH2:15][OH:16])=[CH:9][CH:8]=1)[CH3:5]

Participants

4

Reactant 1

HCID 592539632-[4-(2-Benzyloxyacetylamino)phenoxy]propionic acid methyl ester

Product 1

HCID 592539602-[4-(2-Hydroxyacetylamino)phenoxy]propionic acid methyl esterYield 36.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-[4-(2-Benzyloxyacetylamino)phenoxy]propionic acid methyl ester 68 (15 grams, 43.7 mmol) was dissolved in methanol (150 ml) in a pressure vessel, palladium on carbon (5%, 8 g) added and the mixture stirred under a hydrogen atmosphere (2.5 Kg) for 10 hrs. The catalyst was removed by filtration and the methanol distilled off. The crude 69 was recrystallised in chloroform:hexane (1:6) to give pure 69 (4 g, 36.3%) as a white powder. M.p: 111-112.6° C.

Workup

  1. customThe catalyst was removed by filtration
  2. distillationthe methanol distilled off
  3. customThe crude 69 was recrystallised in chloroform:hexane (1:6)

Sources & evidence

ORD record
ord-168917623d2e4150ae0c18fd5451bd27
Source dataset
uspto-grants-2015_06
Patent number
USRE045548E1

Reaction notes

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